1119-60-4

Usage

Uses

Used in Chemical Synthesis:
6-Heptenoic acid is used as a key intermediate in the synthesis of various organic compounds. Its unique structure with a double bond at the 6th position allows for specific chemical reactions that can lead to the formation of different molecules.
Used in Pharmaceutical Industry:
6-Heptenoic acid is used as a building block for the preparation of pharmaceutical compounds. One such application is in the synthesis of 6-(iodomethyl)-hexanolide through iodo-lactonization, which can be further utilized in the development of drugs targeting specific medical conditions.
Used in Electrochemistry Research:
Due to its electrochemical properties, 6-Heptenoic acid is used in the study of electrode surfaces and the development of new electrochemical techniques. The understanding of its oxidation behavior on Pt(111) electrode surfaces can contribute to advancements in the field of electrochemistry and energy storage systems.

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 4230, 1985 DOI: 10.1021/ja00300a025Tetrahedron, 51, p. 4991, 1995 DOI: 10.1016/0040-4020(95)98696-FTetrahedron Letters, 24, p. 4439, 1983

Synthesis

synthesis of 6-Heptenoic acid and higher homologs of this ω-unsaturated acid, a study of the pyrolysis of wheptano lactone was undertaken. The lactone was prepared by the oxidation of cycloheptanone under Baeyer-Villiger conditions. The pyrolysis of ω-unsaturated acid was effected by dropping the substance under a nitrogen atmosphere into a heated column packed with glass beads.Synthesis of 6-Heptenoic Acid

Precautions

Incompatible with strong oxidizing agents, strong acids and bases.

InChI:InChI=1/C7H12O2/c1-2-3-4-5-6-7(8)9/h2H,1,3-6H2,(H,8,9)

Upstream product

• 2549-59-9 7-methyl-2-oxepanone 
• 30964-00-2 hept-6-ynoic acid 
• 821-57-8 7-chloroheptanoic acid 
• 4475-07-4 2-(Penten-5-yl)malonic acid 
• 539-87-7 oxocan-2-one 
• 821-41-0 5-Hexen-1-ol 
• 151-50-8 potassium cyanide 
• 140-89-6 potassium ethyl xanthogenate 
• 81536-61-0 1,2,6-tribromohexane 
• 124-38-9 carbon dioxide 
• 374073-29-7 6,7-dibromoheptanoic acid 
• 30043-41-5 (hex-5-enyl)magnesium bromide 
• 38858-74-1 (bicyclo[4.1.0]heptan-1-yloxy)trimethylsilane 
• 15250-10-9 1-hydroperoxy-2-methylcyclohexanol 

Downstream Products

• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 2931-10-4 2-ethylcyclopent-2-en-1-one 
• 129266-47-3 benzyl hept-6-enoate 
• 5288-67-5 2-(6-carboxyhexyl)cyclopentanone 
• 186807-26-1 (S)-2-(4-Hept-6-enoylamino-benzoylamino)-pentanedioic acid di-tert-butyl ester 
• 206867-02-9 N-(5-hexenylcarbonyl)-N'-benzyl-N-(4-methoxybenzyl)iminodiacetic acid diamide 
• 321983-75-9 hept-6-en-1-oyl-L-valine-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester 
• 601473-00-1 2-debenzoyl-2'-O-tert-butyldimethylsilyl-3'-de-tert-butoxycarbonyl-3'-hept-6-enoyl-7,10-ditriethylsilyldocetaxel 
• 601472-99-5 C₆₃H₁₀₃NO₁₃Si₃ 
• 204711-93-3 4S-benzyl-3-(6-heptenoyl)-oxazolidin-2-one 
• 367259-36-7 (S,S)-2-(2-cyclohexyl-2-hept-6-enoylaminoacetyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester 
• 920324-09-0 2-phenyl-1,3-dioxan-5-yl 5-formylpentanoate 
• 596111-57-8 N-benzyloxy-α-(4-penten-1-yl)-β-lactam 

Relevant academic research and scientific papers

INTRAMOLECULAR CYCLOADDITION AND SEQUENTIAL RING EXPANSION

Free radical expansion of fused-cyclobutanones gives bicyclic ketones expanded by three and four carbons, with the carbonyl group β to the ring junction.Four-carbon ring expansion shows stereoselectivity favoring the trans-fused product 6-trans.The radical precursor cyclobutanones are readily prepared by intramolecular cycloaddition of ketenes or keteniminium salts to olefins.

A short synthesis of (±)-alloyohimbane via a thioisomunchnone based intramolecular dipolar-cycloaddition reaction

Thioisomunchnone dipoles were generated by the reaction of bromoalkenoyl chlorides with thioamides. The intramolecular dipolar-cycloaddition reaction was used for a short synthesis of the yohimbanoid alkaloid (±)- alloyohimbane.

Hypervalent λ(n)-iodane-mediated fragmentation of tertiary cyclopropanol systems

The oxidation of tertiary cyclopropyl silyl ethers with hypervalent λ(n)-iodanes caused fragmentation which produced alkenoic acids or esters.

Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes

The biocatalytic oxidative tandem decarboxylation of C7–C18dicarboxylic acids to terminal C5–C16dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11-dodecadiene (0.49 g L–1). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C6–C11ω-alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4-pentadiene; scale-up allowed the isolation of 1,15-hexadecadiene and 1,11-dodecadiene; the system represents a short and green route to terminal dienes from renewable dicarboxylic acids.

Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method

Experimental activation parameters for the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene have been measured, and the Monte Carlo-Jumping between Wells/Stochastic Dynamics [MC(JBW)/SD] method, which gives relative free energies of activation, was tested as a means to predict stereoselectivities. The predictions are compared to experimental results, and to predictions from quantum and molecular mechanics methods.

A Highly Catalytic and Selective Conversion of Carboxylic Acids to 1-Alkenes of One Less Carbon Atom

An equimolar mixture of a carboxylic acid and acetic anhydride produces a reagent combination that undergoes a highly efficient decarbonylation/dehydration at 250 deg C using either Pd- or Rh-based catalyst systems, affording excellent yields of the corresponding 1-alkenes of one less carbon atom.

New alkaloidal metabolites from cultures of entomopathogenic fungus Cordyceps takaomontana NBRC 101754

Two new alkaloidal metabolites, cordytakaoamides A (1) and B (2), as well as, 2-[(2-hydroxyethyl) amino] benzoic acid (3) and 2E-decenamide (4), and three known compounds (5–7) were isolated from ethyl acetate and n-butanol soluble portions of the entomopathogenic fungus, Cordyceps takaomontana NBRC 101754. Compounds 3 and 4 were isolated here for first time from natural resources. The chemical structures were established depending upon spectroscopic techniques such as 1D, 2D NMR, and HRMS. The absolute configuration of 1 and 2 was elucidated via the total synthesis of 1 as well as the experimental circular dichroism. Compound 3 was confirmed by a signal crystal X-ray analysis.

Synthesis of unsaturated dibasic acid esters from five-, six-, and seven-membered cycloalkanones

A new route to diesters of symmetrical octene-, decene-, and dodecenedioic acids was proposed. The ratio of the cis/trans-isomers was 1:4. The synthesis involved oxidative splitting of five-, six-, and seven-membered cycloalkanones with hydrogen peroxide into the corresponding ω-alkenoic acids followed by esterification and metathesis over Re2O7/B 2O3-Al2O3-SnMe4.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.

Ni-Catalyzed Carboxylation of Unactivated Alkyl Chlorides with CO2

A catalytic carboxylation of unactivated primary, secondary, and tertiary alkyl chlorides with CO2 at atmospheric pressure is described. This protocol represents the first intermolecular cross-electrophile coupling of unactivated alkyl chlorides, thus leading to new knowledge in the cross-coupling arena.